Enzymes in Organic Synthesis. 41. Stereoselective Horse Liver Alcohol Dehydrogenase Catalyzed Reductions of Heterocyclic Bicyclic Ketones

Article abstract of DOI:10.1021/jo00243a004

Preparative-scale horse liver alcohol dehydrogenase catalyzed reductions of racemic cis and trans bicyclic O- and S-heterocyclic ketones proceed with high enantiomeric selectivity.The diastereotopic selectivity for the pro-R faces of the carbonyl groups is also very high.The ee's of all but one of the product alcohols are >97percent.The ee's of the recovered ketones are in the 52-60percent range.The results confirm that an ether-oxygen or -sulfur substituent does not alter the enzyme's overall structural specificity or stereospecificity toward its ketone substrates.